Charge control agent and related art

Abstract

A charge control agent having a compound represented by the formula shown below as the active ingredient, as well as a method of controlling the charge of resin powder using the charge control agent, and a toner. X: an oxygen atom or N—H; Each of R 1 to R 4 : a hydrogen atom, a carboxyl group, an aminocarbonyl group having or not having a substituent, an aminocarbonylmethyl group having or not having a substituent, an alkoxycarbonyl group, an alkyl group, a phenyl group having a substituent or not having a substituent, or a group that forms a saturated or unsaturated ring having or not having a substituent in cooperation with any other group selected from among R 1 to R 4 .

1 . A toner for developing electrostatic images, which comprises a resin for toner, a coloring agent, and a charge control agent having a compound represented by the following General Formula (I) as the active ingredient: 
       
         
           
           
               
               
           
         
         in Formula (I), 
         X represents an oxygen atom or N—H, 
         each of R 1  to R 4  independently represents: 
         a hydrogen atom, 
         a carboxyl group, 
         an aminocarbonyl group having or not having a substituent, 
         an alkoxycarbonyl group, 
         an alkyl group, 
         a phenyl group having a substituent or not having a substituent, 
         a naphthyl group having a substituent or not having a substituent, or 
         a group that forms a saturated or unsaturated ring having or not having a substituent in cooperation with any other group selected from among R 1  to R 4 , 
         at least one of said R 1  to R 4  in Formula (I) represents said aminocarbonyl group having or not having a substituent. 
       
     
     
         2 . The toner of  claim 1 , wherein the compound of General Formula (I) above is 1 or 2 or more selected from among the following compounds 1 to 6: 
       
         
           
           
               
               
           
         
         in Compounds 1 to 6, 
         each of R 5  to R 34  independently represents a hydrogen atom, an alkyl group, a phenyl group having a substituent or not having a substituent, or a naphthyl group having a substituent or not having a substituent, 
         each of the aforementioned phenyl group having a substituent and the naphthyl group having a substituent has 1 or 2 or more selected from among alkyl groups, cycloalkyl groups, halogen atoms, sulfonic acid ester groups, aryl groups, acylamino groups, arylcarbonylamino groups, aminocarbonyl groups, alkoxy groups, acyl groups, or arylcarbonyl groups as substituents on the aromatic ring thereof; provided that 2 or more substituents are present, they may be mutually identical or different. 
       
     
     
         3 . The toner of  claim 1 , wherein at least one of said R 1  to R 4  in Formula (I) represents a phenylaminocarbonyl group having or not having a substituent, or a naphthylaminocarbonyl group having or not having a substituent. 
     
     
         4 . The toner of  claim 1 , wherein X in Formula (I) represents an oxygen atom. 
     
     
         5 . The toner of  claim 3 , wherein X in Formula (I) represents an oxygen atom.